Hydrochloric Acid → (3aR, 7R,7aR)-4,4-diphenyl-7-fluoroperhydroisoindole hydrochloride

HRID 2399992Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2399992
C(OC([N:8]1[CH2:16][C@@H:15]2[C@@H:10]([C@H:11]([F:29])[CH2:12][CH2:13][C:14]2([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:9]1)=O)(C)(C)C.[ClH:30]>O1CCOCC1>[ClH:30].[C:23]1([C:14]2([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:13][CH2:12][C@@H:11]([F:29])[C@@H:10]3[C@H:15]2[CH2:16][NH:8][CH2:9]3)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 54399787(3aR, 7R,7aR)-2-t-butoxycarbonyl-4,4-diphenyl-7-fluoroperhydroisoindole

Produkt 1

HCID 67746156(3aR, 7R,7aR)-4,4-diphenyl-7-fluoroperhydroisoindole hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

A solution of 2.25 g of (3aR,7R,7aR)-2-t-butoxycarbonyl-4,4-diphenyl-7-fluoroperhydroisoindole in 25 cm3 of dioxane is treated with a 5.8N solution of hydrochloric acid in dioxane and stirred for 2 hours at 20° C. and then concentrated to dryness under reduced pressure (2.7 kPa). The residue is concentrated by adding 100 cm3 of isopropyl oxide, the solid is filtered and dried to give 1.8 g of (3aR,7R,7aR)-4,4-diphenyl-7-fluoroperhydroisoindole hydrochloride, in the form of a cream-colored powder. Proton NMR spectrum (DMSO-d6): 1.0-1.35 (mt, 1H of CH2 in 6); 4.9 (broad d, J=50, 1H, CHF); 7.1 to 7.5 (mt, 14H, aromatics); 9.05 and 9.9 (2 mf, 2×1H, NH2+).

Aufarbeitung

  1. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  2. concentrationThe residue is concentrated
  3. additionby adding 100 cm3 of isopropyl oxide
  4. filtrationthe solid is filtered
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-9ca560f141ff48769de5734b5bf4892d
Quelldatensatz
uspto-grants-1995_09
Patentnummer
US05451601

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